Sulfuric Acid → HCID 66911094, compound

HRID 1967564Notes

Reaction equation

HRID 1967564 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10](O)([CH3:12])[CH3:11])[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.S(=O)(=O)(O)O.[OH-:19].[Na+].[C:21](#[N:23])[CH3:22]>>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([NH:23][C:21](=[O:19])[CH3:22])([CH3:12])[CH3:11])[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 1118Sulfuric Acid2×HCID 6342Acetonitrile3×HCID 14798Sodium HydroxideHCID 581382652-Cyclopropyl-α,α-dimethyl-4-pyrimidinemethanol2×

Product 1

HCID 66911094HCID 66911094, compoundYield 41%

Conditions

Temperature
95 °C

Procedure

Heat a solution of acetonitrile (150 mL) and 2-(2-cyclopropyl-pyrimidin-4-yl)-propan-2-ol of (8.85 g, 50 mmol) to 90° C. In a separate reaction vessel, cool acetonitrile (50 mL) to 0° C. and add sulfuric acid (11.9 mL, 223 mmol) at such a rate that the temperature does not exceed 10° C. Add the cooled sulfuric acid solution to the heated solution of 2-(2-cyclopropyl-pyrimidin-4-yl)-propan-2-ol and acetonitrile and stir at 95° C. for 4 days. Cool to room temperature and add aqueous 5N NaOH (100 mL). Extract the aqueous layer with ethyl acetate (3×). Concentrate under reduced pressure the combined organic layers to yield N-[1-(2-cyclopropyl-pyrimidin-4-yl)-1-methyl-ethyl]-acetamide (4.5 g, 41%) as a yellow oil. MS (m/z): 220.0 (M+H)+.

Workup

  1. customIn a separate reaction vessel
  2. customdoes not exceed 10° C
  3. temperatureCool to room temperature
  4. extractionExtract the aqueous layer with ethyl acetate (3×)
  5. concentrationConcentrate under reduced pressure the combined organic layers

Sources & evidence

ORD record
ord-9f8e24502b7442c5b8f599c10a7707d7
Source dataset
uspto-grants-2013_04
Patent number
US08420654B2

Reaction notes

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